Bikepacking the Punishing Landscapes of the Oregon Outback Trail

This article first appeared on The Field, an online magazine devoted to good design and the great outdoors. Read the original post here.

Around this time last year, I received an email from a friend in Oregon. He and some pals were planning to ride the Oregon Outback Trail in mid-June, and I was invited. (Bend, Oregon-based Hydro Flask would make sure it went off without a hitch.) Knowing nothing of the trail, I wavered until I finally agreed without doing my research. Weeks ahead of departure, I was already in over my head. This would become a theme for the six-day, 364-mile journey.

On June 9 I found myself aboard a southbound Amtrak speeding toward Klamath Falls, near the California border, knowing that in hours I’d turn right around and ride north with sights set on Washington State. The crew consisted of myself, one old friend, and two new. None of us had really bikepacked before, but the concept was growing in popularity by the day and we were curious.

We knew we’d see lots of elevation gain and loss, incredibly lush forests, high desert plains, stunning geological formations, volcanic landscapes, and a hundred different colors of soil. What we didn’t know was that we’d also encounter a rare weather pattern that would replace the expected upper-80s temperatures with low 40s and high 30s—and rain, sleet, wind, and more rain. A lot of Type II fun was had.

The Oregon Outback Trail is a true test of will, endurance, and strength. While my lungs never left me huffing or puffing, my mind experienced rifts of doubt unlike anything I’d known before, and my legs were totally shot by day three. Nevertheless, we persisted. Because that’s what you do when you’re with an encouraging crew led by posi vibes and stronger riders. And when you’re quite literally in the middle of nowhere with no exit available.

Despite the difficulty, it was the people we met along the way, and the incredible kindness of strangers, that made our trip memorable. Stumbling across a community fundraiser with local folk musicians and brisket piled high only hours from the trailhead; pitching tents in a barn to stay out of the cold just minutes after meeting the owner at a bike shop that served beer; sharing drinks and many laughs with an eighth-generation Oregonian on land his great-grandfather had homesteaded more than a century ago; getting crucial touring advice from an aging hippy with a homemade bicycle who hadn’t owned a car since the ’70s.

These are the memories that shine so much brighter than the time I lay in the rain, totally exhausted, wishing the hills would end.

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